Winchester Real Estate | Winchester Properties between $400,000 and $500,000 for Sale

Very unique commercial property located in the heart of downtown Winchester! This versatile property consists of two separate buildings, a large private parking lot, and convenient rear alley access, offering numerous possibilities for an owner-user or investor. The front building has been nicely up-fitted and is currently configured as professional office space. However, the building's original character and functionality remain hidden above the drop ceiling, including tall ceilings and exposed metal trusses. Previously used as warehouse space, the building once featured a dock door for deliveries, making it a great candidate for conversion back to warehouse, showroom, flex, or mixed office/warehouse use. The rear building features a concrete floor, tall ceilings, and excellent potential. It is currently divided into two separate warehouse spaces, providing flexibility for multiple tenants, storage, business operations, or future redevelopment. With two buildings, ample on-site parking, alley access, and flexible commercial space, this downtown Winchester property offers a unique opportunity with a variety of potential uses. Property Highlights: -Large warehouse space in convenient location -Professional office space -Buyers could parcel this property separately -Adjacent to Downtown Winchester, ample retail, and high-density residential

26 N Highland St, Winchester

$484,900

4 Beds ⋅ 3 Baths ⋅ 26022505 MLS

Modern luxury meets everyday living in this beautiful new construction ranch home in Winchester's Fairholme Estates- where thoughtful details, timeless finishes, and incredible golf course view sunsets come together effortlessly. Inside, an inviting open-concept layout features vaulted ceilings and a fireplace anchoring the spacious living room. The timeless kitchen is designed to be both beautiful and functional, with quartz countertops, a charming nook perfect for a coffee bar, a spacious walk-in pantry with floating shelves, and a wine cooler. Just off the kitchen, a dedicated dining space with a vaulted ceiling creates the perfect setting for everything from nightly dinners to effortless entertaining. The private primary suite is a true retreat, featuring a spa-like en-suite with a soaking tub, tiled walk-in shower, dual vanities, and a spacious custom closet. A split-bedroom design provides added privacy, with three additional bedrooms and two full bathrooms offering plenty of space for family, guests, or a home office. Step outside to enjoy the covered back patio to relax or entertain with friends and family. And the location? Hard to beat. Just outside charming downtown Winchester, you're minutes from local shops, restaurants, and everything the community has to offer, with quick access to I-64 for an easy commute. The tall garage provides the perfect solution for vertical storage, adding even more functionality to this thoughtfully designed home.

410 Fairholme Way, Winchester

$450,000

26022780 MLS

Prime commercial opportunity in an ideally located area of Winchester! This versatile commercial building offers an excellent location for an established business, growing company, or investor seeking a property with strong potential. Conveniently situated with easy access to major roadways and surrounding communities, the property provides excellent visibility and accessibility for customers and clients. The building offers flexible space that can be adapted to a variety of business uses. Whether you're looking to establish your business, expand your operations, or add to your investment portfolio, 1320 Fulton Road presents an outstanding opportunity in a desirable Winchester location. Don't miss the chance to make this well-positioned commercial property your next business venture or investment!

1320 Fulton Rd, Winchester

$489,000

4 Beds ⋅ 4 Baths ⋅ 26022723 MLS

Welcome home to this 4 bedroom, 3.5 bathroom home offering plenty of room to spread out. The open kitchen and living room create a comfortable gathering space, while a separate dining room provides additional space for meals and entertaining. The fully finished basement offers even more living space, including a room with a closet that could provide flexibility for a home office, hobby room or potential 5th bedroom depending on your needs. Step outside to enjoy the nice back deck and fire pit area, perfect for relaxing or entertaining. With versatile living spaces both inside and out, this home offers plenty of room to make it your own. Property is under contract with a 48 hour kick out in place.

1137 Lafayette Blvd, Winchester

$450,000

26022173 MLS

Prime commercial opportunity in an ideally located area of Winchester! This versatile commercial building offers an excellent location for an established business, growing company, or investor seeking a property with strong potential. Conveniently situated with easy access to major roadways and surrounding communities, the property provides excellent visibility and accessibility for customers and clients. The building offers flexible space that can be adapted to a variety of business uses. Whether you're looking to establish your business, expand your operations, or add to your investment portfolio, 1320 Fulton Road presents an outstanding opportunity in a desirable Winchester location. Don't miss the chance to make this well-positioned commercial property your next business venture or investment!

1320 Fulton Rd, Winchester

$410,000

4 Beds ⋅ 2 Baths ⋅ 26021961 MLS

*Seller has accepted a contingent offer with a 24 hour kickout.* Welcome to this inviting brick ranch in the desirable Stoney Brook neighborhood! Step inside through the foyer, where you'll find a formal dining room and a beautifully updated formal living room featuring fresh paint and wainscoting. The kitchen opens to the cozy living room/den with a masonry fireplace, making it a great space to relax or gather with friends and family. Just off the living area is a climate-controlled sunroom filled with windows and natural light, with direct access to the backyard and semi-permanent fencing. Down the hall are three bedrooms and a full guest bath that has been refreshed with new paint, beadboard and chair rail, plus a spacious primary bedroom with its own private bath. With a mix of hardwood, tile, carpet and vinyl flooring throughout and an attached two-car garage, this home has plenty of space, charm and potential to make it your own!

406 Lynnway Dr, Winchester

$498,000

4 Beds ⋅ 3 Baths ⋅ 26019848 MLS

Discover the perfect blend of privacy, comfort, and country elegance on nearly 6 acres of beautiful Kentucky land. This stunning 4 bedroom, 2.5 bath home offers the lifestyle buyers dream of — complete with a sparkling inground pool, generous outdoor space, and thoughtful updates throughout. Set in a peaceful rural setting yet conveniently located just 8 minutes from the Winchester Bypass and 15 minutes from Mt. Sterling, this property delivers the best of both worlds: tranquility and accessibility. From the inviting living spaces to the expansive grounds ideal for relaxing, entertaining, or simply enjoying the view, this home is truly one of a kind. Opportunities like this don't come often — this one will move fast. Don't miss your chance. Call today to schedule your private showing.

1780 Stoner-Ephesus Rd, Winchester

$495,000

2 Beds ⋅ 2 Baths ⋅ 26019713 MLS

Don't miss this rare quadruplex opportunity in Winchester. Featuring four units (443, 445,447 and 449 Oxford Drive), this property is perfect for investors seeking multiple income streams in one location. Each unit offers a similar layout with approximately 1,054 ft, 2 bedrooms, and 1.5 baths. The photos shown are from one updated unit, and all units have comparable layouts—making this an ideal setup for consistent rental demand. The vacant property (449) can be viewed through scheduling via showing time and sentrikey box is on the back door, the other 3 units are occupied and can be viewed with 48 hours notice given to the tenants.

443 Oxford Unit 443,445,447,449, Winchester

$429,000

3 Beds ⋅ 2 Baths ⋅ 26018911 MLS

Nestled on 8.9 picturesque acres just off Boonesboro Road, this one-of-a-kind property offers the perfect blend of character, privacy, and endless potential. Whether you're dreaming of a horse farm, hobby farm, or simply room to roam, this beautiful property provides plenty of space for horses, livestock, gardening, or enjoying peaceful country living. Inside, you'll find a spacious open-concept kitchen that flows into a stunning vaulted-ceiling living room, where a floor-to-ceiling rock fireplace creates a warm and inviting focal point. Expansive windows fill the home with natural light while framing beautiful views of the surrounding acreage. The thoughtfully designed layout features 3 bedrooms and 2 full bathrooms, including a private second-floor primary suite that offers a peaceful retreat from the rest of the home. Just off the back of the home, the sunroom is the perfect place to enjoy your morning coffee or relax while taking in the sunset over your property. The basement offers over 1,350 square feet of unfinished space and is already plumbed for an additional full bathroom, providing endless possibilities for future expansion. Whether you envision additional bedrooms, a second living area, a game room, home gym, or the ultimate entertaining space, it's ready for your personal touch. If you've been searching for a property that offers acreage, character, and room to grow, this rare opportunity is one you won't want to miss. Schedule your private showing today!

1024 Flanagan Station Rd, Winchester

$435,000

26002170 MLS

This versatile mixed-use property offers a rare opportunity to combine business potential with built-in residential income. Formerly operated as a neighborhood market, the commercial building spans over 3,000 square feet and is thoughtfully equipped with a full kitchen and laundry area, making it ideal for a wide range of business concepts. Whether you envision a café, restaurant, retail shop, office space, event venue, service-based business, or creative studio, the layout and infrastructure provide a flexible foundation ready to be reimagined. With strong visibility and a neighborhood presence, this property is well-positioned for an owner-operator or investor seeking adaptability and long-term value. Adding to its appeal is the separate 3-bedroom residential home located at 35 Hays, which is currently income-producing and leased through 2027. This creates an immediate revenue stream while you develop, occupy, or lease the commercial space a powerful advantage for offsetting costs or maximizing returns. Opportunities like this offering commercial flexibility, residential income, and long-term potential are increasingly rare. Whether you're expanding a business, launching something new, or investing with vision, this property delivers the space, structure, and upside to make it happen.

35-37 Hays St, Winchester

$413,000

3 Beds ⋅ 3 Baths ⋅ 26009517 MLS

Welcome to this beautiful brick ranch on a basement in Hampton Manor. The double front doors open into a large entry way where you will find a living room with large windows allowing for great lighting. The dining room has a fireplace and exposed beams. The kitchen features updated appliances and granite counter tops with an island and a pantry. The sink overlooks the back yard that backs up to a wooded area. The 2 car garage is right off the kitchen allowing for easy accessibility to bring your groceries in. The primary is on the first floor and has an en-suite with a separate sink area from the shower and toilet. There are two other bedrooms and another full bath on the first floor for guests. In the basement you will find the family room and another gas fireplace. There is enough room to have one corner of the basement be an office if needed. You will also find another half bath and utility room on the lower level. The back side of the basement has a large unfinished area with tons of possibilities. The basement family room has walk up/walk out access to the back yard patio where you will find an above ground pool, greenhouse, play set and trampoline (all can be conveyed if needed).

20 Edgewood Dr, Winchester

$445,500

3 Beds ⋅ 3 Baths ⋅ 26009944 MLS

This is a perfect home for EVERY season.....enjoy multiple, interior gathering spaces and the glow and warmth of either the L R or Dining Room fireplace on the main level or the coziness of the mesmerizing fireplace in the lower level family room during the winter. Watch the backyard come alive with rich and lush vegetation during the Spring from the large, glass walled sun room. For Summer, tons of options await you with the covered front porch, the partially covered back deck or escape to the seclusion of the covered, separate structure at the back. Both the front and back yards are landscaped with many mature trees and perennials that require little attention during Spring, Summer and Fall. Inside, this expansive floor plan packs a lot of punch with a number of interior spaces with an easy flow. The wide entry hall foretells of large room sizes and fresh, neutral paint throughout. The newly renovated kitchen with light wood cabinets is timeless in it's appeal and the adjacent breakfast area is full of natural light. Another handsome fireplace in the next space, with built in shelves could easily function as a D R or Den and the sunroom gives a panoramic view of the beautiful back yard. Three bedrooms and two baths round out the first floor. The lower level features a massive two car garage, half bath, laundry and a large Family Room/Man Cave space for quiet reading or lively entertaining with a third fireplace. So many beautiful options await you in this wonderful home, located in a quiet, attractive, safe and neighborly enclave.

42 Mockingbird Valley Rd, Winchester

$435,000

3 Beds ⋅ 2 Baths ⋅ 26011126 MLS

This 3 bedroom 2 bath ranch home is tucked away in a beautiful wooded area of Clark County. It is sitting on over 10 acres of land that would be great for livestock or hunting. It is just minutes from historic downtown Winchester. The property is also a short drive to retail shops, restaurants, and other amenities. Come take a look at the beautiful view from the front porch of this home in the country.

287 Logan Lick Rd, Winchester

$500,000

20111871 MLS

Visibility, Access, Utilities on site per seller/per plat-buyer to verify, zoned B-3. 1.52 acres located at I-64 exit 96, Right in front of the Hampton Inn, buyer to verify and satisfy themselves to all aspects and information on property. and inspections sold as is. Buyer to Check with all utilities companies to very water electric and gas availability and locations on all utilities.

1005 Early Dr, Winchester

$400,000

22007107 MLS

Great opportunity to buy and build just off the Winchester Bypass. This property is nicely located in the midst of a great deal of new development including a brand new, state-of-the-art CHI Saint Joseph Health Center. Other new development in the immediate area includes Clean Sweeps and Domino's Pizza. Additionally, Walmart and Kroger are located directly across the Bypass from this site. See enclosed Conceptual Development Plan that shows how a standard-sized fast food restaurant with drive thru would fit on this lot. Property Highlights: - Surrounded by area retail - Could be paired with offering at 205 Codella Dr. - Conceptual development plans illustrate QSR with drive-thru

145 Codella Dr, Winchester

$490,000

25508043 MLS

Discover a rare opportunity in downtown Winchester with this assemblage of four vacant lots being sold together as a single offering. Zoned L1 and totaling approximately 1.53 acres, this property presents exceptional potential for redevelopment, infill housing, multiunit residential, mixeduse, or commercial concepts in a central location. Situated just steps from local shops, restaurants, services, and community amenities, these lots deliver true walkable convenience while providing a sizable footprint rarely available in the heart of Winchester. The level terrain and cleared condition simplify planning and construction, giving developers, builders, and investors flexibility to pursue a range of uses aligned with L1 zoning allowances. Whether you're looking to create new housing opportunities, a boutique retail destination, or a thoughtful mixeduse project that contributes to downtown vitality, this assemblage invites strategic vision and development. With accessible infrastructure and a strong community backdrop, 33-41 Winn Avenue is a compelling site for those ready to build in one of Kentucky's vibrant small towns.

33-41 Winn Ave, Winchester

$420,000

3 Beds ⋅ 2 Baths ⋅ 26015824 MLS

Welcome to 187 Hawthorne Drive, a beautifully maintained brick home in one of Winchester's most sought-after neighborhoods. Offering convenient one-level living, this 3-bedroom, 2-bath home features an inviting open floor plan that's perfect for everyday living and entertaining. The spacious living room is anchored by a cozy natural gas fireplace with gas logs, creating a warm and welcoming gathering space. The eat-in kitchen features a breakfast bar and includes a brand-new refrigerator and a quiet new garbage disposal. Recent updates throughout the home provide both style and peace of mind. Gorgeous hardwood flooring has been added to all three bedrooms, and tile flooring has been installed to replace the previous vinyl in the laundry room, pantry, and hallway. The private primary suite is thoughtfully situated on its own side of the home and features an updated shower insert. Enjoy relaxing mornings with coffee or peaceful summer evenings on the screened-in back porch, where you can take advantage of the outdoors without the bugs. Plenty of storage is available with an extra garage closet, pull-down attic storage, and an extra-high crawl space that's ideal for storing lawn equipment, seasonal items, or outdoor tools. The sellers have also invested in ensuring the crawl space remains dry and well protected. Additional upgrades include an HVAC system, updated closet shelving throughout the home, and natural gas service installation. If you're searching for a move-in ready home in Winchester, KY with one-level living, modern updates, excellent storage, and a desirable location close to shopping, dining, schools, and everyday conveniences, 187 Hawthorne Drive is one you won't want to miss.

187 Hawthorne Dr, Winchester

$455,000

8 Beds ⋅ 4 Baths ⋅ 26004961 MLS

Great investment opportunity in downtown Winchester! This spacious quadplex has been updated throughout and offers a true turn-key multi-family property. Each unit features two bedrooms, one bathroom, a full kitchen, and its own private laundry area. Utilities are separately metered, allowing tenants to handle their own services and helping keep operating costs manageable. With a total of 8 bedrooms, 4 bathrooms, and approximately 5058 square feet, this property provides strong rental potential in a convenient location close to downtown shopping, dining, and local amenities. The units are clean, well-maintained, and ready for new tenants, making this an excellent option for investors seeking a solid income-producing property. Schedule your showing today before this opportunity is gone!

265 S Highland St, Winchester

Winchester Properties between $400,000 and $500,000 for Sale

Newest Winchester Properties between $400,000 and $500,000 for Sale

Amanda Marcum - MARCUMsold

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